TOTAL SYNTHESIS OF OPTICALLY-ACTIVE MONOCROTALINE, A CARCINOGENIC PYRROLIZIDINE ALKALOID POSSESSING AN 11-MEMBERED RETRONECINE DILACTONE

被引：28

作者：

NIWA, H

OGAWA, T

OKAMOTO, O

YAMADA, K

机构：

[1] Department of Chemistry, Faculty of Science, Nagoya University, Chikusa, Nagoya

来源：

TETRAHEDRON | 1992年 / 48卷 / 48期

关键词：

D O I：

10.1016/S0040-4020(01)88350-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A total synthesis of the natural enantiomer of monocrotaline (1), a representative of carcinogenic pyrrolizidine alkaloids having an 11-membered retronecine dilactone was achieved through regioselective coupling of (+)-retronecine (3) and the optically active protected necic acid 8, the latter being prepared enantioselectively from the meso-diester 11.

引用

页码：10531 / 10548

页数：18

共 54 条

[41] PYRROLIZIDINE ALKALOIDS - ABSOLUTE CONFIGURATION AT C-2 IN MONOCROTALIC ACID
ROBINS, DJ
CROUT, DHG
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (09): : 1334 - &
[42] PYRROLIZIDINE ALKALOIDS . STEREOCHEMISTRY OF MONOCROTALIC AND TRICHODESMIC ACIDS
ROBINS, DJ
CROUT, DHG
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (10): : 1386 - &
[43] ROBINS DJ, 1992, J NAT PRODUCTS, V9, P313
[44] SYNTHETIC AND BIOLOGICAL STUDIES OF COMPACTIN AND RELATED-COMPOUNDS .4. TOTAL SYNTHESIS OF (+)-COMPACTIN
ROSEN, T
HEATHCOCK, CH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (12) : 3731 - 3733
[45] PLANT SOURCES OF HEPATOTOXIC PYRROLIZIDINE ALKALOIDS
SMITH, LW
CULVENOR, CCJ
[J]. JOURNAL OF NATURAL PRODUCTS, 1981, 44 (02): : 129 - 152
[46] MONOCROTALINE - PYRROLIZIDINE ALKALOID
STOECKLIEVANS, H
[J]. ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1979, 35 (JAN): : 231 - 234
[47] HIGHLY DIASTEREOSELECTIVE ALCOHOLYSIS OF SIGMA-SYMMETRICAL DICARBOXYLIC-ACID ANHYDRIDES USING 1-PHENYL-3,3-BIS(TRIFLUOROMETHYL)PROPAN-1,3-DIOL
SUDA, Y
YAGO, S
SHIRO, M
TAGUCHI, T
[J]. CHEMISTRY LETTERS, 1992, (03) : 389 - 392
[48] STUDIES OF C-SUBSTITUTED TARTARIC ACID .I. PREPARATION OF OPTICALLY ACTIVE 2-METHYLTARTARIC AND 2,3-DIMETHYLTARTARIC ACID
TATSUMI, S
IZUMI, Y
IMAIDA, M
FUKUDA, Y
AKABORI, S
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1966, 39 (03) : 602 - +
[49] IMPROVED PROCEDURE FOR PREPARATION OF OPTICALLY-ACTIVE 3-HYDROXYGLUTARATE MONOESTERS AND 3-HYDROXY-5-OXOALKANOIC ACIDS
THEISEN, PD
HEATHCOCK, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) : 2374 - 2378
[50] TOTAL SYNTHESIS OF D,L-FULVINE AND D,L-CRISPATINE
VEDEJS, E
LARSEN, SD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (10) : 3030 - 3032

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